The odds of any one track being played is .17% not .0017% (40/23000=.0017).

The odds of one of those 40 being played at any time are ~7%.

So, over infinite plays, one of those 40 songs should have been played about every 15 listening sessions.

But, again, just like you could flip a coin a hundred times and come up with a hundred tails, randomness can only tell you the chance, not predict the outcome of any given limited trial.